Woodbine Winners is an inside look at how horseplayers and bettors – from novices to pros – strike gold when playing the races at Woodbine. As part of the ongoing Woodbine Winners series, we're going to show you tickets that result in life-changing scores, get insights into how the bets were made and learn more about the people who hit those winning tickets. 

The Super Hi-5 wager is a very tough bet to hit, and requires the total package when it comes to betting on horse racing: astute handicapping, skill in constructing a ticket, and, of course, luck.

To win the bet, you have to pick the top five finishers in a race. The Super Hi-5 is not a bet that’s offered in every race; it’s usually reserved for races with large fields and is often a feature wager on the last race of a day’s card.

Such was the case at Woodbine in race 10 on Saturday, Aug. 6, when 12 fillies and mares who had yet to win a race squared off in a seven-furlong race on turf.

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Adding intrigue to Woodbine’s Super Hi-5 – called the Jackpot Hi-5 – is that the full pool is paid out only if there is one winning ticket. If there isn’t a single winner, the majority of the wagering pool is carried over into the next race where the bet is offered. On Aug. 6, the Jackpot Hi-5 featured a carryover of more than $93,400 from Aug. 5 heading into the day’s wagering. Woodbine is renowned for their fan- and horseplayer-friendly low minimums, and their Jackpot Pick-5 bet can be played for only 20 cents, with a 15% takeout.

This day, a single bettor put $80 total into a ticket and made a bold decision up front: using one horse – and a longshot at that – as the top selection. The bettor used the same five horses in the runner-up and third-place slots and then added two more for fourth and fifth.

The 20-cent base ticket was constructed as follows (use ABR’s handy gambling calculator as a guide): 1/5,6,7,12,13/5,6,7,12,13/2,5,6,7,10,12,13/2,5,6,7,10,12,13

Retail Therapist, the filly used at the top of the Jackpot Hi-5 ticket, had made five prior starts to Saturday’s race with her best finish coming in her second start back in November 2021, when she checked in fourth. In her two most recent starts, one on Woodbine’s synthetic Tapeta track and one on turf, she finished a combined 30 ½ lengths out of first.

That past performance line made the Tourist filly a 26.30-1 longshot when she exited the gate from the inside position Saturday, but she didn’t run like it, and perhaps adding blinkers helped her improve. After saving ground under jockey Keveh Nicholls, Retail Therapist swung out on the far turn and spurted to the lead in early stretch, rolling to a two-length win. Kimono Kate was second as the 3-1 favorite, and the next three finishers carried odds of 8.50-1, 10.60-1, and 3.40-1.

Putting a longshot on top made all the difference in this Jackpot Hi-5 ticket, and the bettor was rewarded with the entire pool merging the carryover and Saturday’s added money: $134,439.74.